#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009018.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2009018
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  1707
_journal_page_last  1710
_publ_section_title
;
Four N-(2-hydroxybenzylidene)aniline derivatives
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Burgess, John'
  'Fawcett, John'
  'Russell, David R.'
  'Gilani, Syeda R.'
  'Palma, Vitor'
_chemical_formula_sum  'C13 H10 N2 O3'
_chemical_formula_weight  242.23
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  12.413(2)
_cell_length_b  5.744(2)
_cell_length_c  15.597(3)
_cell_angle_alpha  90.00
_cell_angle_beta  97.69(2)
_cell_angle_gamma  90.00
_cell_volume  1102.1(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  190(2)
_exptl_crystal_density_diffrn  1.460
_diffrn_ambient_temperature  190(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  O1  .54835(15)  .3848(3)  .58302(11)  .0375(5) Uani d . 1 . O
  O2  -.0664(2)  -.3197(4)  .3827(2)  .0641(7) Uani d . 1 . O
  O3  -.0557(2)  -.0124(4)  .30437(15)  .0620(7) Uani d . 1 . O
  N1  .38402(15)  .0876(3)  .55492(12)  .0283(5) Uani d . 1 . N
  N2  -.0201(2)  -.1408(4)  .36442(15)  .0423(6) Uani d . 1 . N
  C1  .5984(2)  -.1429(4)  .71461(15)  .0296(5) Uani d . 1 . C
  H1  .5669(2)  -.2866(4)  .72293(15)  .036 Uiso calc R 1 . H
  C2  .6962(2)  -.0878(4)  .7624(2)  .0337(6) Uani d . 1 . C
  H2  .7300(2)  -.1924(4)  .8029(2)  .040 Uiso calc R 1 . H
  C3  .7440(2)  .1256(4)  .74967(14)  .0320(6) Uani d . 1 . C
  H3  .8105(2)  .1631(4)  .78138(14)  .038 Uiso calc R 1 . H
  C4  .6937(2)  .2826(4)  .69041(15)  .0313(5) Uani d . 1 . C
  H4  .7262(2)  .4259(4)  .68311(15)  .038 Uiso calc R 1 . H
  C5  .5945(2)  .2283(4)  .64134(14)  .0269(5) Uani d . 1 . C
  C6  .5449(2)  .0116(4)  .65362(13)  .0252(5) Uani d . 1 . C
  C7  .4411(2)  -.0536(4)  .60645(14)  .0273(5) Uani d . 1 . C
  H7  .4146(2)  -.2029(4)  .61364(14)  .033 Uiso calc R 1 . H
  C8  .2811(2)  .0221(4)  .51168(14)  .0279(5) Uani d . 1 . C
  C9  .2270(2)  -.1851(5)  .5266(2)  .0352(6) Uani d . 1 . C
  H9  .2581(2)  -.2890(5)  .5685(2)  .042 Uiso calc R 1 . H
  C10  .1277(2)  -.2353(5)  .4792(2)  .0355(6) Uani d . 1 . C
  H10  .0913(2)  -.3722(5)  .4892(2)  .043 Uiso calc R 1 . H
  C11  .0829(2)  -.0795(4)  .4169(2)  .0319(6) Uani d . 1 . C
  C12  .1332(2)  .1284(4)  .4021(2)  .0355(6) Uani d . 1 . C
  H12  .1011(2)  .2324(4)  .3606(2)  .043 Uiso calc R 1 . H
  C13  .2323(2)  .1786(4)  .4503(2)  .0319(5) Uani d . 1 . C
  H13  .2667(2)  .3188(4)  .4416(2)  .038 Uiso calc R 1 . H
  H1A  .479(3)  .342(6)  .560(2)  .072(11) Uiso d . 1 . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  O1  .0375(10)  .0283(9)  .0432(10)  -.0034(8)  -.0069(8)  .0080(8)
  O2  .0426(12)  .070(2)  .074(2)  -.0218(11)  -.0154(10)  .0067(12)
  O3  .0501(12)  .0579(14)  .0690(14)  .0062(11)  -.0253(11)  .0057(12)
  N1  .0267(10)  .0279(11)  .0299(10)  -.0008(8)  .0026(8)  -.0012(8)
  N2  .0286(11)  .0484(15)  .0475(13)  .0033(10)  -.0036(9)  -.0056(11)
  C1  .0291(12)  .0273(12)  .0336(12)  -.0001(10)  .0082(9)  .0047(10)
  C2  .0332(13)  .0362(14)  .0309(12)  .0026(11)  .0018(10)  .0055(11)
  C3  .0292(12)  .0374(14)  .0286(12)  -.0009(10)  .0008(9)  -.0043(10)
  C4  .0329(12)  .0252(12)  .0359(13)  -.0038(10)  .0049(10)  -.0021(10)
  C5  .0298(12)  .0245(12)  .0264(11)  .0007(9)  .0037(9)  -.0017(9)
  C6  .0238(11)  .0253(12)  .0272(11)  .0004(9)  .0058(9)  -.0030(9)
  C7  .0270(11)  .0248(12)  .0311(11)  -.0011(9)  .0071(9)  -.0015(10)
  C8  .0273(11)  .0293(12)  .0276(11)  .0004(10)  .0055(9)  -.0049(9)
  C9  .0315(12)  .0410(15)  .0319(12)  -.0046(11)  .0003(10)  .0080(11)
  C10  .0309(12)  .0359(14)  .0396(13)  -.0068(11)  .0052(10)  .0007(11)
  C11  .0234(11)  .0358(14)  .0362(13)  .0012(10)  .0030(9)  -.0067(11)
  C12  .0334(13)  .0340(14)  .0372(13)  .0081(11)  -.0014(10)  .0026(11)
  C13  .0333(12)  .0264(12)  .0358(13)  .0010(10)  .0041(10)  -.0007(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C5 . 1.351(3) ?
  O2 N2 . 1.229(3) ?
  O3 N2 . 1.227(3) ?
  N1 C7 . 1.286(3) ?
  N1 C8 . 1.413(3) ?
  N2 C11 . 1.466(3) ?
  C1 C2 . 1.374(3) ?
  C1 C6 . 1.402(3) ?
  C2 C3 . 1.387(4) ?
  C3 C4 . 1.379(3) ?
  C4 C5 . 1.395(3) ?
  C5 C6 . 1.413(3) ?
  C6 C7 . 1.446(3) ?
  C8 C13 . 1.391(3) ?
  C8 C9 . 1.401(3) ?
  C9 C10 . 1.381(3) ?
  C10 C11 . 1.382(4) ?
  C11 C12 . 1.381(4) ?
  C12 C13 . 1.384(3) ?